Hydrogen Bromide → HCID 13146271, compound

HRID 464012Notes

Reaction equation

HRID 464012 reaction equation
[C:1]([O:4][CH2:5][C:6]([C@:8]1([OH:30])[CH2:25][C:24]2[C:23]([OH:26])=[C:22]3[C:13]([C:14](=[O:28])[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:21]3=[O:27])=[C:12]([OH:29])[C:11]=2[CH2:10][CH2:9]1)=[O:7])(=[O:3])[CH3:2].[Br:31]Br.C12OC1CCCC2.Br>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[Br:31][CH:10]1[CH2:9][C@@:8]([C:6](=[O:7])[CH2:5][O:4][C:1](=[O:3])[CH3:2])([OH:30])[CH2:25][C:24]2[C:23]([OH:26])=[C:22]3[C:13]([C:14](=[O:28])[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:21]3=[O:27])=[C:12]([OH:29])[C:11]1=2

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 9246Cyclohexene oxideHCID 24408BromineHCID 13146269HCID 13146269, compound

Product 1

HCID 13146271HCID 13146271, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

Treatment of 9(R)-acetoxyacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione (3.5 g) with bromine (3.41 g) was effected in a refluxing mixture of chloroform (875 ml) and carbon tetrachloride (1750 ml) with heating for 3 hours, while the reaction mixture was irradiated with 500 W lamp as radical reaction initiator in the presence of cyclohexene oxide (2.51 g) as a scavenger of the generated HBr. The solvent was removed under reduced pressure and ether (52.5 ml) was added to the residue. The resultant mixture was stirred at room temperature for 1.5 hours and precipitated crystals were filtered to give reddish orange powders of 7-bromo-9(S)-acetoxyacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione. M.P., 173°-175° C.

Workup

  1. temperaturewith heating for 3 hours, while the reaction mixture
  2. customThe solvent was removed under reduced pressure and ether (52.5 ml)
  3. additionwas added to the residue
  4. customprecipitated crystals
  5. filtrationwere filtered

Sources & evidence

ORD record
ord-dfde503aff2f48e4bc94888923d2c284
Source dataset
uspto-grants-1985_10
Patent number
US04545936

Reaction notes

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